#8 chukka or #8 ptb mainly for casual wear but dressing up sometimes?
I'd lean towards the #8 PTB, but that depends on your current Alden situation. With summer on the horizon the PTB is a great go to shoe. Either way you will be very satisfied with your purchase.

I know I am being a hypocrite here, but here goes:
Does Alden carry a last which has more width in the forefoot, and less at the heel?
11D in barrie/trubalance works for me, but I think my true size would be a 10.5 B/E. Would a different last fit better? Modified perhaps?

I know I am being a hypocrite here, but here goes:
Does Alden carry a last which has more width in the forefoot, and less at the heel?
11D in barrie/trubalance works for me, but I think my true size would be a 10.5 B/E. Would a different last fit better? Modified perhaps?
Modified does but you will have a bitch of a time getting it fitted.

I've had the Alden Winn Perry "little tanks" for just over a month now and something strange is happening with the leather toe part of the crepe sole. It seems to be warping/bending away from its crepe partner. Right now it's only happening on the left shoe. Has anyone heard of or seen this happening before? Sorry about the shitty iphone pics.
Right shoe for comparison:

Seems to be a common complaint on the crepe sole, which is why I have been shying away. If you do a search for crepe sole in this thread, you will see similar issues. Its a shame really because seems like they are really comfortable from the few times I have tried them on. Sorry to hear you are having a similar problem.